[Ciubba]

I'm trying to propose a mechanism for the following reaction:

https://s3.postimg.io/pmlt4od8j/organic_q.png

I feel like the second step in my proposed mechanism is not very likely to happen, but I can't think of any other way to get the product. Could someone give me a hint?

[AWK]

I do not comment your path of reaction, but you product contains 2 hydrogen atoms more that are  added to a double bond formed during rearrangement.

[Ciubba]

Whoops, I typed the product out wrong both times. The double bond is actually supposed to be there. I've edited my opening post to include the corrected image.

https://s3.postimg.io/pmlt4od8j/organic_q.png

[AWK]

Now stoichiometry is OK.
Are you planning catalyst (CrCl₂) in your reaction?

[Ciubba]

Now stoichiometry is OK.
Are you planning catalyst (CrCl₂) in your reaction?

This is a problem from my textbook (Advanced Organic Chemistry by Lewis), so I imagine that the reaction is as written i.e. no catalyst.

[orgopete]

I'm trying to propose a mechanism for the following reaction:
I feel like the second step in my proposed mechanism is not very likely to happen, but I can't think of any other way to get the product. Could someone give me a hint?

It looks plausible to me. That's how I would have written it.